12 of the Hardest Questions Venture Capitalists Will Ask You

Fundraising? Make sure you know how to answer some of the toughest questions VCs will throw at you..

What Is Your Hole?

“The classic VC role is that of an interrogator, trying to break you for a key secret. But it doesn’t have to be that way. Folks who watch the TV show “Shark Tank” know this feeling. Time after time, a well-rehearsed entrepreneur goes through his pitch, and everyone loves it. But the Sharks (VCs) keep poking at the startup until they finally find a hole. Maybe the company has zero revenue, a poor growth strategy or a weak CEO. Know your weaknesses better than your strengths. Before our first VC meetings, my team sat down and asked each other “gotcha” questions until we were all experts.”

How Are You Different?

“With proper due diligence and competitive analysis, you should be able to make a case for how you differ from other folks in the marketplace. How can you prove that you have a truly unique value proposition? What is it about your offering, your approach, your technology and your team that makes your company able to achieve and execute on this opportunity? “

How Much Is Your Company Valued at?

“The reason why determining the valuation of your company is so difficult is because there is no right answer. On the one hand, you need to be realistic, but on the other hand, you do not want to undervalue your company, as the VC may think something is wrong. The best way to handle this question, and most others that arise when negotiating with a VC, is to do all you can to have several VCs interested in your company. Like in most negotiations, if you have several interested parties, they may bid against each other, which will allow you to obtain the best terms for you and your company.”

What’s Your Customer Acquisition Cost?

“The best way to tackle this question is to show reasonable estimates for customer acquisition, using well-researched numbers and reasonable conversion rates. If you can’t explain how you are going to acquire customers for less than what you sell them on average, at a fundamental level, you have failed to explain your business.”

When Are You Paying Me Back?

“There are many entrepreneurs with amazing ideas. Ideas are a dime a dozen, but execution is everything. Every investor will ask you when and how he will recoup his investment. What experience do you have? What is your track record? Before going into a meeting with a VC, make sure to tell him about your experience, your track record and, most importantly, how you will recoup his money. Lots of people pitch the idea before the finances. Pitch the finances and how the VC will make money; if he asks you a question, then you got him to bite — now it’s all about your elevator pitch.”

Why Won’t a Huge Corporation Build Something Like This?

“VCs will ask, “Why won’t a huge corporation build something like this and use their existing customer base and capital to capture market share?” The best way to defend against this is to have technology and intellectual capital that the company will want to acquire, rather than destroy. “

Why Hasn’t This Worked Before?

“Zaarly raised $14.1 million in a Series A in fall of 2011. But it was a question earlier that spring from Marc Andreessen in our pitch meeting that gave our founding team the most pause, “Why do you think this hasn’t worked in the past?” We didn’t have a great answer — more of a hunch really that mobile technology didn’t exist to allow distribution of information in real time previously. But the question forced us to examine our predecessors who had tried and failed to learn what landmines to avoid. Our lesson: Know your landscape and learn from prior failures and success. “

How Do You Define Success for Yourself and Your Company?

“VCs want to invest in founders who are dedicated to “hitting a home run.” If you’re satisfied with building a small company, that’s a big red flag for VCs. As we’ve all heard, a number of founders have said yes to exits their VCs wanted them to say no to. Other founders have taken the middle ground by cashing out some of their shares to secure their personal finances, and then continued to go big. Either way, VCs want to invest in founders who are focused on a disruptive, game-changing product/idea. This is a vital point to keep in mind as you consider whether funding is right for you.”

Do You Know [Insert Company]? Why Not?

“Anytime a VC throws out the name of a potential competitor that you don’t know or haven’t looked into, it can throw you off balance for a minute. The fact is, it may be a company that you don’t think is a viable competitor, so you don’t know much about it. The best way to tackle it: Tell them the truth, “We looked at our key competitors and that company did not meet the criteria. But we’ll look into it further after this meeting.” The key is to maintain control of the conversation because it shows you can handle a curveball. “

What Is Your Plan To Grow?

“The most difficult thing to explain to an investor is your plan to grow. They want to know how you’ll outdo everything you’ve already done. Prep by picturing your future: What staffing or product creation will help you have the business you want to have?”

Why Haven’t You Gotten Traction?

“The best way to handle that question is by not approaching VCs until you have achieved traction. Venture capital should be looked at as an accelerator for existing success, not as a runway extender to get it right.”

Debt or Equity?

“Many investors will know going into a deal whether they want preferred stock or a convertible note. Sometimes, however, they will leave it up to the company. Angel investors, in particular are likely to leave it up to the company as the more sophisticated party. For the company, this is an opportunity to maximize the value of the investment, but they must also be wary of getting off on the wrong foot with the investor by being overly aggressive or appearing uninformed. A crash course in VC deals and a good deal lawyer will make sure you maximize the former and mitigate the latter. “

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.